Patent GB-306859-A (GB)
Title: Process for the manufacture of copper ammine complex azo compounds
IPC: C09B45/01
Filed: 1927-11-21
Abstract: 306,859. Carpmael, A., (I, G. Farbenindustrie AKT. Ges.), Nov. 21, 1927. Azo dyes, soluble copper compounds of; azo dyes, forming on the material.-Copper ammine complex azo compounds applicable as dyes and insecticides are obtained by coupling a diazo, diazoazo, or tetrazo compound containing one or more carboxyl-, hydroxyl-, or carbonyl-groups in o-position to one or more azo or diazo groups with a coupling component in the presence of a water-soluble complex nitrogenous copper compound such as 'The following examples are specified :-(1) The dyestuff 2-aminonaphthalene-3-carboxylic acid (2 mols.) # urea of 2: 5: 7-acid is formed in the presence of [Cu(NH3)4]SO4, H2O; [Cu{N(CH3)3 }4]SO4 and [Cu(pyridine)4SO4 may be also used. (2) The dyestuff 4: 6-dichloro-2- amino-1-hydroxybenzene # #-naphthol is formed in presence of [Cu(NH3)4]SO4 or [Cu(NH2CH3)4]SO4. (3) The dyestuff 2-aminobenzoic acid (2 mols.) # 5 : 5<1>.dihydroxy-2 : 2<1>- dinaphthylamine-7 : 7<1>-disulphonic acid is formed /(en)2 in presence of [Cu ]SO4 (where en= \(H2O) ethylene diamine), glycocoll copper diammine, [Cu(pyridine)4]SO4 or [Cu(NH3)4]SO4. (4) The dyestuff 2-aminobenzene-5-sulphonic acid# #-naphthol is formed in presence of [Cu(NH3)4] SO4 or [Cu(NH3)4] (OH)2. (5) The dyestuff 3- amino benzaldehyde # urea of 2 : 5 : 7-acid - 2-aminobenzoic acid in which the second coupling takes place in presence of [Cu(NH3)6]Cl2 or [Cu(NH3)4]SO4. (6) The dyestuff 4 : 4<1>-diamino, diphenylurea-3 : 3<1>-dicarboxylic acid 2- phenylamino-5-hydroxynaphthalene - 7 - su1pbonic acid (2 mols.) is formed in presence of (Cu(NH3)4]SO4, benzidine - 3 : 31 - dicarboxylic acid # 1-hydroxynaphthalene-4-sulphonic acid /(en)2 (2 mols.) in presence of [ Cu ]SO4 \(H2O)2 (Cu(NH2CH3)4]SO4 or [Cu(pyridine)4]Cl2; J-acid, 1-ethoxy-8-hydroxynaphthalene-3: 6-disulphonic acid or acetyl-H-acid may partly or wholly replace phenyl-J-acid in this example. The dyestuff 5-nitro-2-aminobenzoic acid # phenyl-J-acid formed in presence of (Cu(NH3)4] SO4 is reduced and converted into the urea. (7,) The dyestuff 2-aminobenzaldehyde or 2-amino-1- hydroxybenzene (2 mols.) -- 5 : 5<1>-dibydroxy- 2 : 2<1>-dinaphthylamine-7 : 71-disulphonic acid is formed in presence of [Cu(NH3)4]SO4. Specification 245,128 is referred to. (8) The dyestuffs anthranilic acid # 2-(4<1>-aminobenzoyl)-amino- 5-naphthol-7-sulphonic acid and 4-nitro-2-diazophenol-2-(4<1>-aminobenzoyl)-amina-5-hydroxynaphthalene-7 -sulphonic acid formed in presence of tetramine cupric sulphate, diazotized on the fibre and coupled with #-naphthol, give red and bordeaux shades respectively. (9) The dyestuff 4- chlor-2-aminobenzoic acid # 2-(3<1>-aminobenzoyl)-amino-5-naphthol.7-sulphonic acid is diazotized on cotton and developed with #-naphthol in presence of tetrammine cupric sulphate. (10) Red shades are obtained when the dyestuff anthanilic acid (1 mol.) # urea of 2: 5: 7-acid formed in presence of tetrammine cupric sulphate is developed on the fibre with diazotized p-nitraniline. Glycocoll copper diammine is prepared by dissolving glycocoll copper in an excess of ammonia. Tetra-trimethylammine-copper sulphate is prepared by adding an excess of trimethylamine to aqueous copper sulphate. Tetra- (monomethylamine)-copper sulphate is prepared from methylamine and copper sulphate. Copper pyridine chloride [Cu(pyridine)4]Cl2 is prepared from cupric chloride and pyridine.